Phytosterols are a class of polycyclic polyisoprenoids compounds biogenetically derived from isoprene units. For practical purpose, the term “phytosterol” and “polycyclic polyisoprenoid” are used interchangeably in the present invention. The most important of these—sterols, sapogenins, phytosterols, and terpenoids—have structures similar to plant and animal steroids, which have a basic structure of three linked six-membered rings and one five-membered ring. Steroids and terpenoids with hydroxyl groups have names that end in “ol,” such as cholesterol and menthol, respectively. A number of these are known to have medicinal properties (Singh et al., Current Science, Vol. 89, No. 2, 269-290 (2005)). Most of these polycyclic polyisoprenoids are known to be water insoluble, which results in their poor bioavailability from any topical compositions.
The present invention relates to sugar esters of said phytosterols, which are conjugates of phytosterols with certain sugar lactones; in their optically active, inactive, or racemic forms (such as d, l, dl, and meso); wherein phytosterol moiety provides the alcohol part, and the sugar lactone moiety provides the carbonyl part of said sugar esters. These esters are useful for the treatment of multiple skin conditions and ailments, including age spots, acne, loss of cellular antioxidants, collagen loss, loss of skin pliability, loss of skin suppleness, skin wrinkles including fine lines, oxidation, damage from radiation, malfunction of matrix metalloproteases, malfunction of tyrosinases, damage from free radicals, damage from UV, dry skin, xerosis, ichthyosis, dandruff, brownish spots, keratoses, melasma, lentigines, liver spots, pigmented spots, dark circles under the eyes, skin pigmentation including darkened skin, blemishes, oily skin, warts, eczema, pruritic skin, psoriasis, inflammatory dermatoses, topical inflammation, disturbed keratinization, skin changes associated with aging, nail or skin requiring cleansers, conditioning or treatment, and hair or scalp requiring shampooing or conditioning, and combinations thereof.
The sugar esters of the present invention are prepared by a novel method, wherein said phytosterols undergo a chemical reaction with certain sugar lactones to form said esters.
This invention also relates to a method of treatment of skin condition and ailment including age spots, acne, loss of cellular antioxidants, collagen loss, loss of skin pliability, loss of skin suppleness, skin wrinkles including fine lines, oxidation, damage from radiation, malfunction of matrix metalloproteases, malfunction of tyrosinases, damage from free radicals, damage from UV, dry skin, xerosis, ichthyosis, dandruff, brownish spots, keratoses, melasma, lentigines, liver spots, pigmented spots, dark circles under the eyes, skin pigmentation including darkened skin, blemishes, oily skin, warts, eczema, pruritic skin, psoriasis, inflammatory dermatoses, topical inflammation, disturbed keratinization, skin changes associated with aging, nail or skin requiring cleansers, conditioning or treatment, and hair or scalp requiring shampooing or conditioning, and combinations thereof.